((1R,2R,3S,6S)-3-Benzyloxy-2,6-dimethyl-7-oxa-bicyclo[4.1.0]hept-2-yl)-methanol

Base Information

Chemical Name:((1R,2R,3S,6S)-3-Benzyloxy-2,6-dimethyl-7-oxa-bicyclo[4.1.0]hept-2-yl)-methanol
CAS No.:188052-30-4
Molecular Formula:C₁₆H₂₂O₃
Molecular Weight:262.349
Hs Code.:

Synonyms:((1R,2R,3S,6S)-3-Benzyloxy-2,6-dimethyl-7-oxa-bicyclo[4.1.0]hept-2-yl)-methanol

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Chemical Property of ((1R,2R,3S,6S)-3-Benzyloxy-2,6-dimethyl-7-oxa-bicyclo[4.1.0]hept-2-yl)-methanol

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Technology Process of ((1R,2R,3S,6S)-3-Benzyloxy-2,6-dimethyl-7-oxa-bicyclo[4.1.0]hept-2-yl)-methanol

There total 11 articles about ((1R,2R,3S,6S)-3-Benzyloxy-2,6-dimethyl-7-oxa-bicyclo[4.1.0]hept-2-yl)-methanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

: 237406-14-3
(1R,2R,3S,6S)-3-Benzyloxy-2,6-dimethyl-7-oxa-bicyclo[4.1.0]heptane-2-carbaldehyde

: 188052-30-4
((1R,2R,3S,6S)-3-Benzyloxy-2,6-dimethyl-7-oxa-bicyclo[4.1.0]hept-2-yl)-methanol

Guidance literature:: With sodium tetrahydroborate; In methanol; for 0.5h; Ambient temperature;
DOI:10.1016/S0040-4020(99)00305-1

Reference yield:

: 115513-10-5
((S)-2-Methoxy-1,5-dimethyl-cyclohexa-2,5-dienyl)-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone

: 188052-30-4
((1R,2R,3S,6S)-3-Benzyloxy-2,6-dimethyl-7-oxa-bicyclo[4.1.0]hept-2-yl)-methanol

Guidance literature:: Multi-step reaction with 7 steps

1: 91 percent / aq. HCl / tetrahydrofuran / 2 h / Ambient temperature

2: 100 percent / NaBH₄, ZnCl₂ / tetrahydrofuran / 1 h / -60 - -15 °C

3: 63 percent / KH, n-Bu₄NI / tetrahydrofuran / 1.) room temp., 24 h, 2.) reflux, 3 d

4: 90 percent / I₂ / tetrahydrofuran; H₂O / 18 h / Ambient temperature

5: 98 percent / DIBAL-H / CH₂Cl₂ / 1.) -10 deg C, 15 min, 2.) 0 deg C, 15 min

6: 99 percent / 1,5-diazabicyclo<5.4.0>undecene-5 / CH₂Cl₂ / 1 h / Ambient temperature

7: 94 percent / NaBH₄ / methanol / 0.5 h / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; iodine; tetra-(n-butyl)ammonium iodide; potassium hydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1016/S0040-4020(99)00305-1

Reference yield:

: 237406-10-9
(2'S,2S)-2,4-dimethyl-2-<<2'-(methoxymethyl)pyrrolidinyl>carbonyl>-3-cyclohexen-1-one

: 188052-30-4
((1R,2R,3S,6S)-3-Benzyloxy-2,6-dimethyl-7-oxa-bicyclo[4.1.0]hept-2-yl)-methanol

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / NaBH₄, ZnCl₂ / tetrahydrofuran / 1 h / -60 - -15 °C

2: 63 percent / KH, n-Bu₄NI / tetrahydrofuran / 1.) room temp., 24 h, 2.) reflux, 3 d

3: 90 percent / I₂ / tetrahydrofuran; H₂O / 18 h / Ambient temperature

4: 98 percent / DIBAL-H / CH₂Cl₂ / 1.) -10 deg C, 15 min, 2.) 0 deg C, 15 min

5: 99 percent / 1,5-diazabicyclo<5.4.0>undecene-5 / CH₂Cl₂ / 1 h / Ambient temperature

6: 94 percent / NaBH₄ / methanol / 0.5 h / Ambient temperature

With sodium tetrahydroborate; iodine; tetra-(n-butyl)ammonium iodide; potassium hydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1016/S0040-4020(99)00305-1